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Building an unparalleled musical legacy, a vibrant career at the top levels of entertainment and a business empire worthy of a Forbes cover isn't easy, but it's not complicated either. In Toby Keith's case, there's genius in the simplicity. His new album Drinks After Work is another perfect example of how a big project like an album – not to mention a seemingly boundless and diverse brand – can be boiled down to a few timeless truths about hard work and good times. Exceptions prove every rule, however, and Keith is certainly not immune to life's harsh realities when the spotlight dims and storm clouds rise – as they did unmercifully in 2013.

The balance of the album celebrates life's peaks, however, and that's no accident as Keith's music has increasingly become a reflection of his live shows. He and his tight band of co-writers – Scotty Emerick, Bobby Pinson and Rivers Rutherford – do most of their work on the road, grabbing guitars and putting words to music during downtime between concerts.

"People ask why we write so many songs about drinking and partying," he says. "Well, when we’re writing, that’s what we’re doing. We’re out on the road working, but we’re festive. If we were stuck in a cabin for a week hunting or something, you might write about being away from the party. But when you're on the road, you've got this crowd and you’re presenting a party to them, it’s really hard not to get caught up in that and keep it fun. I like having a lot of that on my albums; when they turn it on, I want them to smile."

And smile they have, propelling Keith to rarified air as one of the most successful songwriter/artists of all time with more than 80 million broadcast performances of his work and 32 #1 singles. Arguably, he's the most successful self-contained artist in country music history. And that popularity isn't limited by borders as he's toured packed European venues twice in the last few years. He's also preparing for his first tour of Australia, where he is the most-requested American country performer, recently enjoyed several high profile awards nominations and has had four hit albums in the country.

The process that has led to those hits and chart-topping albums wasn't in place from the beginning of his career, though it certainly was foreshadowed by his debut. Written solely by Keith, "Should've Been A Cowboy" rocketed to No. 1 and went on to become the most-played country song of the '90s. And while he continued to have number one after number one on the radio charts, it wasn't until the 1999 release of How Do You Like Me Now?! and concurrent departure from a label with which he was in constant conflict that he began to set a sustainable and incredibly successful creative course.

"We write all year," Toby explains. "And after about 13 years of doing it this way, it's gotten where I know going in that I'll have enough good songs to choose from. I'll spend a week with Rivers, two weeks with Bobby and two weeks with Scotty. Then I'll write some by myself. So you end up with an album-and-a-half's worth of uncut stuff ready to sort and stack. I’m always way ahead."

From the album's opening thump of "Shut Up And Hold On," Keith and co-writer Pinson evoke an arena show feel. The audience appeal is palpable, and the title track only furthers the vibe with perhaps the freshest, most unique sound from Toby in years. The only track he didn't write, the song was an unlikely stab at something very different. "[Label exec] Mark Wright was really high on this 'Drinks After Work' thing, and I didn’t know if I could cut it or not. It’s really out of the norm for me, but I told him I'd give it a run and it bloomed in the studio."

The classic Toby turn-of-phrase in "Little Miss Tear Stain" – "is never still a good time to call?" – the throwback barroom shuffle of "Last Living Cowboy" and the completely unsubtle "Show Me What You're Workin' With" keep the fun rolling. Even the coming-of-age ode "Before We Knew They Were Good," "Whole Lot More Than That" with its arresting couplets and the wry "I'll Probably Be Out Fishin'" are likely to have concertgoers raising red Solo cups in salute.

Plumbing less exuberant musical depths are the steel-drenched broken heart ballad "The Other Side Of Him" and a Toby Keith-first tribute to farmers titled "Hard Way To Make An Easy Living." But those songs only hint at the raw emotions that accompanied the making of this album.

Drinks After Work is dedicated to the memory of Keith's longtime bandleader and bass player Chuck Goff, who passed in February. Three months later, a tornado flattened much of Moore, OK, where the water tower proudly proclaims: "Moore, home of Toby Keith." Among those directly hit were Keith's sister and sister-in-law, who both experienced substantial damage to their homes.

Perhaps the best window into that sense of loss is "Chuckie's Gone," which Keith wrote by himself and included as one of three deluxe edition bonus tracks:

A twister came through our hometown, tore a lot of peoples’ houses downThat always happens in the spring, and this time you missed everything ... Stage goes up, stage goes down, buses roll through another townThere’s words to write and gigs to play and you’ll always be a song awayYour bass is there where you used to stand, and even though we got a killer bandI still look up in the middle of the song and realize Chuckie’s gone

"It really doesn’t change the band as a group because it happened to all of us as a group," Toby says. "Everybody leaned on everybody else. We all lost the same friend out on the road. He was with us 25 years and he was my band leader. He was a really good guy and, at the end of the day, you only get to live it once, so you better live it up while you’re here."

In May, Keith rushed home to Moore from the Nashville studio where he was recording the album to aid in recovery and serve as the face of the community to many in the national media. "I didn’t have but four songs cut when the tornadoes hit, so I was a little late getting the album turned in," he says.

In July, Keith rallied fellow artists Garth Brooks, Trisha Yearwood, Ronnie Dunn, Willie Nelson, Sammy Hagar, his daughter Krystal and more for the Oklahoma Twister Relief concert. Drawing more than 60,000 to the University of Oklahoma stadium, the event raised approximately $2 million.

This year has also seen him producing another project close to his heart – Krystal's Show Dog-Universal debut. "I wrote a few things, she’s written a few things and then she’s written with some of the biggest writers in Nashville," he says. "I’m trying to let her do as much of it on her own as she can. There’s a 25-year age difference, so what works for me may not work for her. So it's great to see her taking the reins and trying to get this thing up and rockin.'"

Other ventures much further along in their growth curve include Keith's I Love This Bar And Grill restaurants and his signature Wild Shot Mezcal. "I’ve learned along the way to only take on things that work with the music," he says. "When I have a new artist on my label that needs to get out and do shows for radio, I can plug them in at the restaurants. Same with Wild Shot. I'll sell it at my shows, I'll sell it in my bars – it won't take me away from what I do the way some kind of unrelated business might."

Instead, Toby will focus his time – often backstage waiting for the show to start – to write a song for the next album. And, ultimately, it's that continuing focus and musical discipline that has elevated his entertainment career as well as ancillary businesses to heights rarely if ever seen.